Day 1: New York City to Livingston Manor to Cochecton (154 miles)
Leave the Manhattan skyline behind on the two-hour drive north on the Palisades Parkway. Hop on NY-17 to enter the Catksills Region, which begins in the scenic former lumber town of Barryville. (Most visitors approach via touristy Woodstock.) Merge onto NY-97 and follow the steep-banked Delaware River that separates New York from Pennsylvania, keeping an eye out for bald eagles riding the thermals. After 30 minutes, you’ll arrive in the tidy town of Narrowsburg, where creative New York City transplants have set up shop on Main Street. Narrowsburg Roasters(25 Main St.; 845/252-6688; breakfast for two $12) was opened by former West Village set designer Will Geisler in 2006. Geisler makes a killer latte, and his biscotti and maple shortbread are addictive. Next door, browse the well-edited collection of housewares—from handwoven Brazilian bedspreads to cowhide chairs, at Nest. Across the street you’ll find Enochian Inc.(55 Main St.; 845/252-3828), a modern custom dress shop, which expanded last year with a men’s line of leather jackets and alpaca sweaters.
Drive northeast for 20 minutes along woodsy NY-52 to the Golden Guernsey(31 Mitchell Pond Rd. E., Cochecton; 845/932-7994; doubles from $125). The former barn is painted bright marigold, decorated with Midcentury furniture, and run by ex-Brooklynite and graphic designer Amy Miller. For supper, follow NY-52 for 45 minutes north and turn off on Shandelee Road toward the fly-fishing town of Livingston Manor, where tackle and taxidermy shops stand alongside galleries and an organic-food market. The (2 Pearl St., Livingston Manor; 845/439-3405; dinner for two $50), a gastro-tavern popular with urban weekenders, serves shepherd’s pie and Beaverkill Brook trout, while seasonal produce like Swiss chard and beets come from the chef’s garden. Back at the Golden Guernsey, finish the evening with a sampling of decadent house-made ice creams such as coffee-bacon and vanilla-rosemary.